When it comes to lobster rolls and New England clam chowder, nobody can touch Massachusetts. Shrouded in history, the Bay state is well known as the birthplace of the American revolution, the Freedom Trail, and the Boston Tea Party. Seafood, history, the Red Sox- Massachusetts has it all. RedAwning will help you find the perfect vacation rental to complete your East Coast experience. Browse your favorite Massachusetts region using the blue location links below, or filter your preferences using the panel on the side. With our simplified booking process, you'll have the most important part of your trip buttoned in no time.

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  1. HOUSE
    Colbyco Oceanside- Scituate

    Colbyco Oceanside- Scituate

    Scituate, MA

    Spectacular Colonial where you wake up to the sound of the waves and unobstructed ocean views! Wake up to the sound of the waves as you take in the unobstructed ocean views! This spectacular newer (2013) colonial features the best in craftsmanship,...

    $696 to $986/night

  2. CONDOMINIUM
    Bentley Brook Studio

    Bentley Brook Studio

    Hancock, MA

    The town of Hancock is off the beaten path near the Taconic Mountains, which are part of the Appalachians. Hancock is 14 miles northwest of Pittsfield, MA, and 28 miles east of Albany, NY. Bentley Brook is tucked away in a peaceful rural setting...

    Pool Hot Tub

    $143/night

  3. HOUSE
    Colbyco CitySide

    Colbyco CitySide

    Boston, MA

    Rare large and comfortable Boston single family home available for vacation or short term rental. It is located in South Boston near the Beach, Convention Center, Seaport District and Downtown Boston. Huge deck with views of city skyline. This home...

    $1,044/night

  4. HOUSE
    Charming 3BR Beach Cottage

    Charming 3BR Beach Cottage

    East Falmouth, MA

    The beach is just steps away from this beautifully remodeled 3-bedroom cottage (just 7 houses from the path to the private association beachfront)! A true Cape Cod home with a high-end kitchen, hardwood floors, a lovely tiled bathroom, and an...

    FREE CANCELLATION

    $126 to $300/night

  5. HOUSE
    C368 Dudek (3-Bedroom Home)

    C368 Dudek (3-Bedroom Home)

    Charlestown, RI

    Beach Pass to Blue Shutters and Charlestown Town Beach. Charming and spacious three bedroom Cape with central air and nice hardwood floors thru out. Large spacious bright living room with wall of atrium doors and windows that welcomes in the gardens...

    $183 to $330/night

  6. APARTMENT
    110 on Parker Hill

    110 on Parker Hill

    Boston, MA

    Mission Hill Apartment, 2 bedroom, 1.5 bathroom, in unit washer dryer, central air/heating on Parker Hill in the Mission Hill Neighborhood. Full kitchen including dishwasher, disposal, coffee maker and pots and pans, Unit is brand new for 2018 and...

    Pets OK

    $107 to $274/night

  7. HOUSE
    Windmill Home Overlooking Marsh

    Windmill Home Overlooking Marsh

    Yarmouth Port, MA

    Take in incredible, ever-changing marsh views from this traditional 4BR home (sleeps 8) in a quiet Yarmouth Port neighborhood. Enjoy the convenience of 2.5 bathrooms in addition to an oversized outdoor shower for rinsing off after the beach. A...

    FREE CANCELLATION

    $319 to $555/night

  8. HOUSE
    Coastal/Beach Access Cottage in Centerville

    Coastal/Beach Access Cottage in Centerville

    Barnstable, MA

    Historic grandeur, quaint seaside energy and a friendly community bring visitors from near and far to the shores of Cape Cod. This renovated 3-bedroom, 1-bath cottage embodies the best of this town by the sea, on a lakefront property in a tranquil...

    FREE CANCELLATION

    $231 to $448/night

  9. HOUSE
    Spacious 5BR Long Pond Home- Private Beach & Dock

    Spacious 5BR Long Pond Home- Private Beach & Dock

    Harwich, MA

    From an abundance of outdoor space to a welcoming interior with breathtaking lake views and fireplaces, this three-story 5BR/4BA home is a sure bet for your Cape Cod getaway. Overlooking Long Pond, this stunning home features a private beach and...

    Pets OK
    FREE CANCELLATION

    $521 to $1,400/night

  10. HOUSE
    New 2BR on Nature Conserve w/ Sun Deck

    New 2BR on Nature Conserve w/ Sun Deck

    Wellfleet, MA

    PROPERTY OVERVIEW Nestled on 24 acres of Massachusetts Audubon and Wellfleet Conservation Trust Land, this brand-new 2BR/1.5 offers a sunroom, expansive balcony, and miles of lovely hiking trails. Spend sun-dappled afternoons in the enormous yard...

    FREE CANCELLATION

    $260 to $378/night

  11. HOUSE
    4BR w/ Private Beach Access

    4BR w/ Private Beach Access

    Eastham, MA

    Situated on a forested property in the highly desirable Dunes Beach Association, your 4BR getaway offers a serene location between the woods and sea. Follow a sandy pathway to enjoy direct access to a glorious semi-private Cape Cod beach. This...

    FREE CANCELLATION

    $252 to $568/night

  12. HOUSE
    2BR Garden Cottage, Near Beach

    2BR Garden Cottage, Near Beach

    Wellfleet, MA

    Enjoy the peaceful surroundings of this 2BR/2BA cottage, less than a mile from the heart of Wellfleet. Those who love the great outdoors will be right at home in the artist’s garden. Indoors, high ceilings and natural light complement an...

    FREE CANCELLATION

    $197 to $372/night

  13. CONDOMINIUM
    2BR Condo at Ocean Edge Resort

    2BR Condo at Ocean Edge Resort

    Brewster, MA

    You can have it all at Ocean Edge Resort & Golf Club. Step out from your 2BR/1.5BA condo and onto the beautiful fairway -- the course was designed by Jack Nicklaus and makes for an incredible backdrop for an afternoon game or a bike ride. Ocean...

    Pool
    FREE CANCELLATION

    $143 to $332/night

  14. APARTMENT
    Brookline Brownstone

    Brookline Brownstone

    Brookline, MA

    This 3 BR 2 BA apartment is fully updated and has in unit laundry. Good for couples, solo adventurers, traveling nurses, doctors, business travelers, families (with kids), and big groups. The apartment is minutes from Longwood Medical Area, home of...

    Pets OK

    $183 to $461/night

  15. APARTMENT
    201 on Washington

    201 on Washington

    Jamaica Plain, Boston, MA

    Wonderfully built brand new 990sq foot 2 bed / 2 bath apartment in Jamaica Plain with patio! Minutes walk to gorgeous Jamaica Pond and the night life on Centre Street, 5 min walk to Subway! Dedicated parking, central air, gas heat, in unit...

    Pets OK

    $74 to $274/night

  16. HOUSE
    Serene 4BR w/ Large Deck & Trail Access

    Serene 4BR w/ Large Deck & Trail Access

    Wellfleet, MA

    This quaint 4BR/3BA is surrounded by tall trees and lush greenery. The Cape Cod Rail Trail (a 22-mile scenic path from Wellfleet to Dennis) is quite literally in your backyard. Just wander past the vegetable patch and hop on the trail! Enjoy a...

    FREE CANCELLATION

    $272 to $488/night

  17. HOUSE
    3BR Gem at Cape Cod Bay w/ Water Views

    3BR Gem at Cape Cod Bay w/ Water Views

    Eastham, MA

    Memorable beach trips begin at this elegant 3BR/3BA Eastham house. With a private master bedroom and separate family suite, there’s plenty of room to spread out. Watch the sun set over Cape Cod Bay from the upper deck, or follow the walking path...

    FREE CANCELLATION

    $869 to $1,037/night

  18. CONDOMINIUM
    Bentley Brook 2 Bedroom

    Bentley Brook 2 Bedroom

    Hancock, MA

    Bentley Brook Surround yourself with the natural beauty of Massachusetts at Bentley Brook. Situated at the bottom of Jiminy Peak in the stunning Berkshires, Bentley Brook is the ski enthusiast dream come true. Ski out your door and straight to the...

    Pool Hot Tub

    $197/night

  19. HOUSE
    Big 4BR Gem w/ Fenced Yard & Private Beach Access

    Big 4BR Gem w/ Fenced Yard & Private Beach Access

    Hyannis, MA

    This spacious 4BR/2.5BA classic Cape Cod abode is located just a 3-minute walk from a private beach. Enjoy quality time with friends and family in three inviting living spaces, or savor alfresco meals on the patio in the big fenced yard. Spend...

    FREE CANCELLATION

    $261 to $653/night

  20. HOUSE
    Barnstable Village 4BR w/ Yard

    Barnstable Village 4BR w/ Yard

    Barnstable, MA

    With a quiet location in an historic Barnstable neighborhood, this 4BR/2BA home offers a wonderful sense of seclusion, though countless local attractions sit right on your doorstep. Walk 1.2 miles to unique shops and restaurants along Main Street....

    FREE CANCELLATION

    $132 to $377/night

  21. APARTMENT
    506 on Parker Hill

    506 on Parker Hill

    Boston, MA

    525 Sq Ft. Mission Hill Apartment, 1 bedroom, 1 bathroom, in unit washer dryer, central air/heating on Parker Hill in the Mission Hill Neighborhood. Full kitchen including dishwasher, disposal, coffee maker and pots and pans, Unit is brand new for...

    Pets OK

    $92 to $229/night

  22. HOUSE
    3BR on Buck’s Pond w/ Beach Access

    3BR on Buck’s Pond w/ Beach Access

    Harwich, MA

    Look out over Buck's Pond from this 3BR/2BA Cape Cod house with water views from almost every room. Your own private beach is just steps away, where you can fish, swim, sail, or just stroll the sandy shore. This home is located in the idyllic...

    FREE CANCELLATION

    $214 to $421/night

  23. HOUSE
    Remodeled 4BR Near Beaches & Golf

    Remodeled 4BR Near Beaches & Golf

    Dennis, MA

    Classic New England charm awaits at this 4BR/2BA Dennis rental, with cedar shingles and a quaint nautical vibe. Spacious interiors and an expansive backyard offer lots of room for nine people to spread out. Throw a frisbee on the lush green lawn,...

    FREE CANCELLATION

    $405 to $603/night

  24. DUPLEX
    3BR w/ Yard & Outdoor Shower- Walk Everywhere!

    3BR w/ Yard & Outdoor Shower- Walk Everywhere!

    Dennis Port, MA

    This single-story 3BR cottage is a quaint getaway offering superb outdoor space. Relax on the front porch and host a fun cookout in the large backyard. An outdoor shower is great for rinsing sandy toes after a fun beach day. Walk across the street...

    FREE CANCELLATION

    $211 to $241/night

  25. HOUSE
    Quaint 4BR Cottage in the Woods

    Quaint 4BR Cottage in the Woods

    Wellfleet, MA

    The tranquil setting at this 4BR/3BA Cape Cod home will put you in full vacation mode. Set on 1.5 acres of land with soaring pine trees, the house is less than 10 minutes from beaches on the ocean and bay. Visit nearby Bound Brook Island Beach for...

    FREE CANCELLATION

    $286 to $506/night

  26. HOUSE
    Classic 4BR on Oyster Pond w/ Dock & Boat Fleet

    Classic 4BR on Oyster Pond w/ Dock & Boat Fleet

    Falmouth, MA

    Situated on the shores of Oyster Pond, this 4BR/3BA 1930s-era summer home radiates classic Cape Cod charm. Amenities include a private dock with rowboats (with sails), a kayak, and canoe for your use. The lake is ideal for swimming and fishing, and...

    Pets OK
    FREE CANCELLATION

    $325 to $658/night

  27. HOUSE
    Moonakis River 4BR w/ Pool & Spa- Near Downtown

    Moonakis River 4BR w/ Pool & Spa- Near Downtown

    East Falmouth, MA

    Enjoy the magnificent water views from inside or out. Beautiful gardens with a waterfall, gunite heated saltwater pool with spa (seasonal), outdoor shower, and pool house with a half bath make this home perfect for outdoor and indoor fun. Launch...

    Pool Hot Tub
    FREE CANCELLATION

    $672 to $991/night

  28. HOUSE
    W091 Vaccaro

    W091 Vaccaro

    Charlestown, RI

    We welcome you to enjoy our family cottage nestled in the woods and just a 10 minutes from the beach. Our place has a large backyard with plenty of shade and privacy. Take advantage of our deck and patio on our one acre lot. Feel free to gather...

    $134 to $210/night

  29. HOUSE
    C384 Buckley

    C384 Buckley

    Charlestown, RI

    Begin making those vacation memories in this seaside cottage . Nicely furnished , this one level home has open kitchen & living area , large deck and an outside shower to rinse off that beach sand . Sleeping accommodations for 6 . Master bedroom has...

    $293 to $324/night

  30. HOUSE
    C315 Broccoli 676

    C315 Broccoli 676

    Charlestown, RI

    Ocean front on Charlestown Beach. Make a lifetime of memories at this newly built beach house. Relax on the deck overlooking the Atlantic Ocean, Block Island, the Breachway and miles of one of South County’s most sought after beaches. Enjoy your...

    $581 to $844/night